Friend of the Devil
by JustMePeyt
Summary: Someone has been targeting friends of the Winchester brothers- threatening them and leaving them with the same message: that whoever is after them is mad and ready to take his anger out on the boys. The brothers discover the man is someone they once knew but is a bit...different than last time they'd met.
1. Chapter 1

_Author's Note: This story takes place towards the end of season 8 of Supernatural, so it may contain spoilers. I want to thank my friend talknerdy2meh for helping me edit, write, and publish this story. You're awesome, bro. Check out her stories because she's pretty freaking awesome. Thanks for giving my fic a chance and feel free to leave any reviews._

Sam and Dean were back in the Impala from meeting the Scribe, Metatron, in Santa Fe, New Mexico back to their Bunker in Lebanon, Kansas. They had left in the early hours of the morning to try to get back in one long drive. Sam was sick and in pretty bad shape and the brothers just wanted to get back to relax and recover in the Bunker.

Sam immediately fell asleep once they started out and slept for about half the trip. When he woke up he didn't talk at all and just stared out the window, lost in his thoughts. Dean let him be, but got annoyed with Sam's dreary mood and decided to try to cheer him up a bit. He glanced at his brother who was leaned against the window and decided to take action.

He turned the radio on and started flipping through stations trying to find a good suit for the moment. He paused on a Top Hits station that was playing some Taylor Swift song and turned the volume up a few notches. Sam glanced over at Dean who hummed quietly to the song. Sam turned back to the window and tuned out the music.

Next, Dean found a station playing some mariachi music, upped the volume some more, and danced along. Sam shot Dean a confused glare and repositioned himself in the passenger seat.

Dean, seeing that his brother was still being disheartening, clicked through more stations, this time turning the volume up as a salute to Nat 'King' Cole's "L-O-V-E." He was going to need something more than just the radio to Sam get Sam to smile, so Dean started singing along.

"L is for the way you look at me," Dean sang, snapping his head towards his brother.

"O is for the only one I see," this time with a jab to Sammy's side.

"V is very, very extraordinary," Dean full out bellowed with a dramatic arm flourish that sent the car swerving.

"Dean, honestly?" Sam said over the music, "C'mon."

"E is even more than anyone that you adore can-"

Sam shook his head and clicked the radio off.

"Aw c'mon, Sammy. It's a classic!"

"Just don't. Please."

"Sorry, Sam. Just trying to lighten the mood," Dean explained. Just as Sam was turning back to the window one of his cell phones started ringing. He gave a short sigh and answered the phone.

Sam's tired face face cleared and was replaced with confusion, then worry. "But you're all right, Garth? Ok good. Sure thing. Bye," Sam hung up. "So that was Garth. Called to tell me he got jumped. By a demon."

"What? Who? Is he alright?"

"He didn't give a name but apparently this demon knows us. Garth said we "know him but have forgotten him" or something like that. He didn't hurt Garth just shook him up a bit. He's using Garth to get a message to us... That he's pissed and will be coming for us."

Dean sat in silence for a minute then, "Who the hell is this son of a bitch?"

"I don't know. Garth was confident that it was a demon that he had never seen, but apparently we have."

"Crowley?"

"We haven't really forgotten about him have we?"

"Ha, I wish," Dean muttered and turned his focus back to the road.

Sam and Dean discussed any other possibilities for who the new demon might be but then the conversation turned to their next plan of action. The priority was to get back to the Bunker and and dig up whatever they could on how to cure a demon and get to finishing the last Trial.

"Where we're heading doesn't sound like a picnic," Dean turned to Sam.

"But we're heading somewhere," Sam nodded, "The end."

Dean turned back toward the dark road and spotted a figure lying in the middle of his lane. He slammed on the brakes and swerved into the other lane to keep from hitting whatever it was. Sam started and braced himself against the dashboard. The Impala's headlights lit the figure with a white light. Sam and Dean jumped out of the car and saw a person covered in a tan trench coat with smears of red.

"Cas?" It couldn't be. He hadn't seen the angel in several weeks and here Dean had almost ran him over.

"A little help here?"

Sam rushed to the Cas's side but Dean hesitated. The last time he saw the angel, Castiel had lied to him, beaten him to a bloody pulp, then fled with the angel tablet without saying a word, and now here he is lying bloody in Dean's path.

But Cas was family, and family helps each other when they're bleeding out so Dean ran to his friend's side and helped him get into the backseat of the Impala. As soon as they got Cas in the car, he fell unconscious. Once they started out, Dean glanced at Cas in the rear view mirror then turned to Sam.

"What do you think happened to him?" Dean asked in a hushed voice.

"No idea. We haven't heard from him since the Crypts," Sam shrugged.

"Think we can trust him? I mean he didn't exactly leave with a nice hug goodbye."

"We should give him a chance at least."

"Yeah. Let him heal then see what's up."

Dean glanced at the speedometer and guessed that they were less than an hour away from Lebanon so he pressed harder on the accelerator to get to the Bunker. Once they got there, Sam and Dean helped Cas in and bandaged him up as best as possible. When they were positive that Cas would be fine, Sam and Dean left him in a spare bedroom then went off to catch a few hours of sleep.


	2. Chapter 2

Dean slid into the Impala and slammed the door shut behind him. He wondered if he was being too hard on Cas, then pushed away the doubt. Cas needs to learn what happens when you betray someone, and what better time than now to teach him.

He started up the Impala, and put her into drive. He was just moving forward when his cell phone rang. He pulled it out of his pocket and looked at the caller ID: _Jody Mills._

"Hello?" He answered.

"Hi, Dean, it's Jody," Jody said in a mixture of fear and confusion, "I, uh, I just had a visitor, well not really he kinda broke my door down, helped himself to a beer, then pinned me against the wall. But other than that he-"

"Jody, Jody, take a deep breath. That's right. Now what did this man say?"

Jody took another deep breath and calmed herself down, "Well, that was the funny thing. He said he had a message for you. He, uh, shit, I can't remember. Something about knowing your dad and some one-Sam! Yes, Sam being in Hell?"

Dean shook his head trying to make sense of it all. Was this the same demon that jumped Garth? It was starting to sound like it and if it was then Dean could narrow down the list to demons that John knew. "Are you okay, Jody? Did he hurt you at all?"

"No, no. Well sort of. He broke my nose and gave me a black eye probably, but nothing too serious. I'll be alright," Jody said without her former hysteria.

"Do you need anything, Sheriff? Is there anything else he said?" Dean was desperate for any more information to narrow down who the demon might be.

"I'm fine, Dean, don't worry about me. I was just a little shaken up. He did want me to tell you that he's working his way towards you and he's mad."

"What about Claire and Alex? Are they okay?" Dean asked referring to the two teen girls Jody had taken under her wing.

"Yeah, they're fine- weren't home when it happened, thank God," Jody explained and was back to her old self.

"Alright, thanks, Jody. Sorry about this, we're still trying to figure out who this is."

"Well when you find out, kick his ass for me, would you?"

Dean chuckled, "Sure thing, Jody. Take it easy."

Dean shut off the Impala and went back into the Bunker- the groceries would need to wait. He walked in as Sam handed Castiel a stack of files from the Bunker's archives. They looked up, surprised. "What is it?" Cas asked.

"Jody Mills called and it sounds like she was visited by the same demon Garth was on Thursday."

"Is she okay?" Sam asked.

"She was a bit hysterical when I answered, but she's fine other than a broken nose and possible black eye."

"But as far as the demon goes, did she give us anything to go off of?"

"Yeah, he mentioned Dad and you in the Cage. Not much else, but she was given the same message Garth had."

Sam nodded. A sudden wave of memories overtook him. Lucifer beating Dean over and over again while Sam struggled to pull the Devil back, getting control of his body again, and pulling Michael, who was wearing Sam and Dean's half-brother, Adam, into the hole then the entire experience of being trapped in Hell with Michael and Lucifer. Sam shook his head to clear the thoughts and turned to Dean, "Okay so so far we know that it's a demon possessing a man, both us and Dad have encountered him, but apparently he's one we've forgotten about."

"And was somehow involved in the Apocalypse," Cas offered.

Sam looked down at his phone which had just vibrated. He opened up a text from an unknown number and read it aloud, his face overcome with worry, " _Charlie Bradbury: Tomorrow. I won't be as nice this time, Sammy."_

"That's got to be him. Sam, can you track down the text at all? I'm gonna call Charlie and tell her to get back here," Dean pulled his phone out and walked to the other side of the room while Cas helped Sam get started on tracking the number.

"Hey, Dean, what's up?" Charlie asked sweetly.

"Charlie, I need you back at the Bunker, now. Just, just be here before tomorrow okay?"

"Dean, what are you talking about? What's the matter?"

"Charlie, you're in danger. A demon is after you and we have no idea who he is or what he's going to do. You'll be safe here, though."

"I'm in St. Louis right now and it'll take me a little less than eight hours to get to Lebanon-"

"That's great. It'll be cutting it closer than I'd like but you'll be okay, Charlie, I promise."

"But, Dean," Charlie said desperately, "I-70 is down to one lane because of road construction. And I'll need to go all the way through St. Louis during rush hour and then through Kansas City... I just don't think I'll make it, Dean."

"We'll get on the road now and speed like hell if you need to, Charlie. I'm not going to let this son of a bitch get you."

"Okay, okay. I'll try. I'll call you once I get out of construction to see where we're at, okay? I'm leaving the convention right now, a particularly expensive one too by the way," Charlie said sternly with an attempt at a laugh, but Dean could hear the anxiety behind it.

Dean turned back to Sam and Cas. Cas looked up from Sam's laptop and explained to Dean, "Sam was able to trace the phone number to St Louis, Missouri. Where is Charlie?"

"Charlie said she's in-" Dean paused as he realized, "St Louis."

Sam's head snapped up, "He must be following her. Smart too. That way he won't need to worry about tracking her down first _and_ he's being led straight to us."

"I could go retrieve her," Cas suggested.

Sam shook his head sadly, "You're too weak. It'd be dangerous for Charlie to tag along with you. That's if you can even fly."

Castiel looked at the floor helplessly, "What do we do then?"

"We let her come," Dean decided in a hard voice, "The demon won't be able to get through the wardings and Charlie will be fine. He said he won't act until tomorrow."

"And we're trusting him? When has that ever stopped a demon, Dean," Sam questioned.

"But yet we continue to do it."

Waiting for Charlie was worrisome for all three of the boys. Cas absently flipped through files and books searching for any tips for the third trial, Sam stared at his computer screen, breaking the silence every so often with a heavy sigh, and Dean made a trip into town, called Kevin to see how the Tablets were coming along, and made a habit of checking in with Charlie every hour to see how the drive was coming along.

The reports were promising: traffic was slow but not as bad as expected. The eighth call didn't bring as positive news. There was a major collision and her estimated time of arrival was now 12:30 Sunday morning.

"There's no way you can get off the interstate?" Sam implored.

"Not for another ten miles and traffic is completely stopped," Charlie said steadily.

Sam sighed and rubbed his eyes, "Okay, well, just be careful, Charlie."

"Yeah, I've basically put salt lines around the whole interior of the car."

"Well, call when you have news. And make it good next time, 'kay?"

"I can only hope. Talk to you later, Sam."

Eleven o'clock call rolled around and there was no answer from Charlie. Dean called her over and over her and left countless messages, but there was nothing. They sat in silence hoping Charlie's phone had died or something and that she would come a-knocking any minute now. Finally Dean announced he was going to take the Impala out and go look for her and Sam and Cas insisted on coming with after being holed up waiting for news all day. Fifteen minutes into the drive and Sam's phone rang with a call from Charlie. He answered it and put it on speaker.

"Charlie? Where are you? Are you okay?" Dean said steadily.

"D-Dean? There's this guy here and he says he wants me to tell you he 'misses you boys, but before he comes to visit he has to stop by and chat with another Winchester buddy _,'"_ Charlie said shakily, "I'm off 181 near Downs. It's definitely a funky tow-"

Charlie had read the _Supernatural_ books and was trying to get a message across to the boys by using one of their code words. Dean caught on immediately and drove like hell to get to Downs. After a quick search, the boys found Charlie's car on the side of an empty road parallel to a thick tree line. With further inspection, they found the car unlocked and Charlie's body slumped in the driver's seat with her neck slit in a fine line.

Sam's shoulders slumped and shook as he turned around and walked back to the Impala. When he leaned on the car, the body sank a foot and creaked under all of his weight. He had lost so many people in his life: friends, family, and now Charlie. They had just gotten to know her well. Sam had just started to think of her as his little sister, but he should have known better. All his family is dead except Dean and even then he's had to live without his big brother before. If Sam wasn't so optimistic they would have left earlier to look for her, but he insisted on waiting, claiming it was only a dead battery. But now Charlie's dead, and it was all his fault.

Dean pinched the bridge of his nose then in a sudden flurry of pent up anger spun around and kicked a tire of Charlie's car and hammered his fist into the roof. He turned away and walked a few paces down the road with his eyes squeezed shut and hands on the back of his head. If only he had left faster. He should have known something was wrong when she didn't answer and now her death was all his fault.

Castiel put his fingers to her forehead in an attempt to heal Charlie, but it was too late and Cas was too weak to heal a paper cut, much less a fatal wound. He guessed that she had been dead for about fifteen minutes, so the demon must have acted and fled as soon as the call cut off. If only Cas was stronger, he would have been able to get Charlie to the Bunker in the blink of an eye, he'd be able to heal her right now. But he couldn't. He couldn't because his grace was occupied trying to fix himself. If only he hadn't been so ignorant to Sam and Dean he would have had the power to save Charlie. But he didn't and it was all his fault.

 _I know I shouldn't have but I did... Forgive me? ~Peyt_


	3. Chapter 3

The boys needed to give Charlie a proper hunter's funeral before they did anything else. They took axes from the back of the Impala and cut down branches from the tree line to make the pyre. Cas found a white canvas sheet stuffed way back in the Impala's trunk and used the sheet to wrap Charlie's body in.

Nothing could be heard but the uneven _thunk'_ s of the axes. They lit the pyre on fire once they had finished and stood in a comfortably numb silence. Everyone was lost in their thoughts. For Dean it was reliving Charlie's greatest hits- their most memorable times they had together. Sam was remembering the countless times in the past where he'd had to go through the same ritual with friends and family: building the pyre, burning the body, and saying goodbye. And Cas, Cas was experiencing something new. He was witnessing humanity's heartbreak at its strongest. The air was dark with sorrow, but beneath it was pinpoints of light- memories of laughter and victories that Castiel realized was all that humans had to hold on to. That little bit of light and hope is all that the Winchesters acquire to get through each day and Cas looked at the boys with a newfound respect and understanding.

As the last flame flickered out and the three got back into the Impala, Dean got a text. _Kevin: five minutes_ it read.

"Dammit!" Dean shouted and hit the steering wheel. He threw the Impala into gear and dialed up Kevin.

After a few rings, he answered, "Hello?"

"Kevin, where are you?" Dean demanded.

"Staying in Danny's Inn in Waldo, Kan-"

"Lock the doors and salt the entrances. There's a demon coming after you."

"Um okay. Who?"

"We don't know, but you've got less than five minutes. We'll be there as soon as we can," Dean explained and hung up.

Cas spoke up from the back seat, "I'm going to get him. It's the fastest way we can get there."

"You can't. You're too weak to bring the two of us with you," Sam said.

"That's why I have to going alone." A moment later there was a rustle of wings and the angel was gone.

"What the hell does he think he's doing?" Dean exclaimed as he sped towards the interstate.

"He _is_ an angel, Dean. He's dealt with demons before."

"We don't know what this demon is capable of yet. Hell, we don't even know for sure it is a demon," Dean argued. He wasn't exactly keen to trusting Kevin's life in the hands of a weak angel.

"All the evidence we have points to a demon, Dean. Oh no," Sam said looking at his phone.

"What?" Dean's tone softened to hopelessness, "What is it?"

" _Castiel: now_."

 _This chapter is a bit shorter than the others. Hope you're enjoying because it's about to get a little more interesting *evil smirk* If you want something more light hearted check out my poem "The Giving Tree- Castiel" and feel free to leave reviews; I always love to hear feedback! ~Peyt_


	4. Chapter 4

_Spoiler: this chapter contains a torture scene. Precede with caution. ~Peyt_

A half hour later, Sam and Dean arrived in Waldo. When they found Kevin's room at Danny's Inn, it was empty. The window was shattered and the room showed signs of a brief struggle. Castiel's destination was Kevin's room, so the demon either finished Kevin before the angel came or was able to overpower both the angel and the prophet. Dean looked in the bathroom and Sam approached the window. There was a yellow sticky note on the air conditioner under the window. Sam picked it up and read it to Dean, "5729 W 73rd Street. I think we passed that street coming in, Dean."

"Well let's go then," Dean decided and snatched the paper from Sam.

Dean felt his phone vibrate from his pocket as they walked out of the motel. It was another text from the demon. Dean opened it up and read it to Sam, "It says ' _See you soon_.'"

Everything was black and Cas felt a cloth pressed to his eyes, blinding him. The air smelled of old wood, hay, and leather leading Cas to assume he was in an old barn. He inhaled deeper and scrunched his nose in disgust; the air reeked of sulfur. He tried to stand up and discovered he was chained to a chair. He ran his fingers over the chains binding him and discovered a complicated sigil designed to prevent angels from fleeing. Cas could hear uneven breathing from someone near him and recognized it as Kevin's.

"Kevin?" Cas whispered.

The prophet moaned in response.

"Are you alright?"

Kevin took a shaky breath, ready to speak, but the words got caught in a fit of coughing. The coughs sounded watery and Cas smelled blood. He pulled against his chains trying to get to Kevin. Cas vowed he wouldn't let anymore of the Winchester's friends die because of him, then sat silently listening for Kevin's breathing.

"Kevin?" Cas called out. There was no answer. No breathing, no coughing, nothing.

Cas strained even harder on his bindings, praying that he'd have enough strength now to heal Kevin; Cas didn't have the same strength as he used to, for most of his power was occupied on healing himself. When the demon jumped him from behind, Cas was embarrassed at how easily the demon won. He left Sam and Dean confident that he'd be back with Kevin safe and sound before the boys had a chance to doubt him, but his confidence had brought the fall of him.

Cas tensed up when he heard footsteps approaching him. "Castiel, good to see you again," a man's voice welcomed sarcastically.

But he wasn't quite a man. He sounded younger, a few years younger than Sam, Cas guessed. Cas also recognized the voice. It was one he hadn't heard in awhile, but it was definitely one he should know.

Cas heard him step closer. He couldn't see, but Castiel could feel the man standing over him. Suddenly Cas felt a cool blade against his throat and he stiffened. "It really has been too long, Cas," the voice said dryly and dropped the blade, cutting deeply down Cas's forearm.

Cas couldn't help it, he yelled out in a mixture of pain and surprise. Only an angel blade could cause that type of pain to him. He pulled and yanked on the chains binding him to the chair. "With these sigils, you won't be going anywhere soon," the demon sneered and carved a circle on the palm of Castiel's hand with the blade. He stopped circling and stabbed the blade forcefully down on Cas's palm.

Cas couldn't help the scream that escaped his lips as he felt the blade pierce through his hand, severing nerves and tendons and breaking bones.

The man reached out and punched Cas. "You think that hurts, little angel?" he sneered and slowly cut down Castiel's other arm, stopping at the wrist and stabbing through the angel's other hand. Cas arched his back and yelled through gritted teeth until he could taste blood. "Because that's nothing compared to what you left me to deal with!" the demon yelled in Cas's face and made a neat slash down the angel's jaw.

"Left you?" Cas asked breathing heavily. He couldn't see but his head spun and eyes drooped, "Who ar-"

The demon interrupted him with a swift cut diagonally across Castiel's chest, exposing the not-quite-healed stomach wound Crowley inflicted onto him. The man noticed the wound and pressed the tip of the blade sharply in the middle of it.

"Ah yes. Naturally you've forgotten about me, Castiel. That's all I seem to get- neglect. From you, my father, those goddamn Winchester's," he yelled, pressing the blade harder into Cas's gut and twisting.

Cas screamed and desperately tried to fit the clues together. When Cas finally got his breathing somewhat under control he took a breath to ask a question but was no sooner interrupted when his captor slowly dragged the blade across the angel's chest that bisected the previous cut, creating an _X_ across Cas's chest.

"Look, Cassy. 'X' marks the spot," the demon grinned and pressed the tip of the weapon at the intersecting point directly above Cas's heart. Cas felt the tip slowly and steadily pressing harder. "No!" Cas yelled but the blade didn't recede until it was moments away from being fatal and without a good hard twist.

"Who are you?" he asked weakly through gritted teeth.

The demon punched Cas again, even harder this time. "2010. Stull Cemetery in Lawrence. Remember?" he said and started slicing and stabbing Cas anywhere and everywhere as he talked. His tone softened suddenly to a sad dejected whisper, "Then later in the Cage when you pulled Sam out, did you ever think to come back for me, too?"

Castiel understood now. Sam and Dean had been wrong about their demon assumption. All the clues were coming together as Cas slowly blacked out. This was no demon.

"Michael."


End file.
